Building Stronger School Communities Through Enrollment and Retention with Benjamin Welbourn

Chalk and Code

In this episode of Chalk and Code, host Theron Davis is joined by Benjamin Welbourn, CEO of Schola, a Phoenix-based edtech platform helping families find the schools that fit them best. What began as a startup helping parents navigate school options has evolved into a full ecosystem, streamlining enrollment, managing community programs, and even using AI to help schools build stronger relationships with families.

Ben shares his own experience as a learner who didn’t feel at home in traditional classrooms, and how that journey shaped his commitment to personalized, student-centered education. From hiking the Appalachian Trail to launching Virto Education and now leading Schola, his story is one of building bridges between students, systems, and meaningful outcomes.

This conversation explores how school choice, AI, community engagement, and human connection intersect and what it takes to make education feel less like a system and more like a fit.

Key Moments

03:47 Global College Pathway Expansion

08:24 Expanding Enrollment Through Extracurriculars

11:23 Improving School Enrollment Practices

14:28 Family School Engagement Strategy

20:13 Prioritizing Psychological Safety in Schools

22:08 Enrollment Challenges and Cycles

24:30 School Consolidation Necessity

28:57 "Real-Time School Engagement Insights"

32:55 Parent-School Connection Challenges

37:07 AI-Powered School Program Recommendations

39:31 Ed Tech Challenges and Growth

41:03 Esser Funds' Aftermath on Schools

47:31 Substance Over AI Hype

Why You’ll Love This Episode

You’ll hear how Benjamin and the team at Schola are flipping the script on traditional K–12 marketing by helping schools build trust, communicate value, and become hubs for their communities. If you're in education, product, policy, or just want to know how schools can thrive in an era of rapid change, this episode offers a playbook for putting families first and using data, tech, and empathy to make it happen.

You’ll walk away with:

• A fresh perspective on school choice and community engagement

• Real examples of how Schola helps schools attract and retain the right students

• Insights into how AI can amplify, not replace, human relationships in education

• Lessons on navigating today’s rapidly shifting education landscape with integrity

Connect with Benjamin Welbourn

• LinkedIn: https://www.linkedin.com/in/benwelbourn
• Breshna: https://home.schola.com/

Connect with Us

• Company’s LinkedIn: https://www.linkedin.com/company/flexion-inc
• Company Website: https://flexion.us/

If this conversation sparked a new idea or challenged your assumptions, share this episode with a colleague and subscribe for more thoughtful discussions at the intersection of learning, leadership, and educational technology.

Join us next time on Chalk and Code, where the science of learning meets modern technology.